I remember the first time i saw someone socks and heels together. It was in a magazine, of course. I stared at each picture for at least ten minutes trying to figure out how I could put together that trend. The particular photo editorial I fell fast for was from teen vogue. I can't remember what issue it was, and I could only find three pictures of the bunch, but here they are:
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I tried wearing socks with a pair of chunky heels I picked up at my local target. Of course I got commentary from the load of girls who always have something to say about what I'm wearing -- the gangster sweatpants girls. I don't know, they sort of humor me.
Some other ways to wear socks and heels:
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Another thing I really like at the moment is leopard print tights thrown under denim shorts. Who knows if this is "in" now, all I know is that when put together with a simple outfit, leopard print tights can make you look off-duty model-esque. See below:
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Image sources: me, teenvogue forums